The movie follows a professional criminal called John Lyshitski as he appears to be still quite frustrated because his plans have failed. This criminal decided to place the son of his victim in prison and return to turn things upside down in front of that victim as much as possible.
Let's Go to Prison feels like an overextended sketch-comedy idea insufficiently filled out by subsidiary characters (few significantly figure) or standout setpieces.
Arnett underplays to the point where he seems as shellshocked as his character, while Shepard seems to have forgotten that the film is supposed to be a comedy.
Los Angeles Times
November 20, 2006
Because the movie can't bring itself to take that leap into full-on absurdity, the characters and comic opportunities stay confined to their cells.
Though sloppily edited like a bad B-movie, this poor man's version of Trading Places will undoubtedly resonate for anyone with a taste for gruesome gallows humor, and a desire to see a spoiled, rich kid get a taste of how the other half lives.
Shepard's character periodically rattles off damning statistics about America's booming prison industry, but most of the gags are of the don't-drop-the-soap variety.